Celebrities hold tremendous influence over American fashion on the red carpet, in the cinema, and on the stage. Garments like Marilyn Monroe's classic white dress in "The Seven Year Itch" have become cultural touchstones that embody the art of the era throughout Entertainment history. What’s more, when you look at images of singers and movie stars, you quickly realize that fashion is a baffling thing: what looked amazing ten years ago may now be hilarious. Regardless of how fashion changes, the celebrities who wore those items remain fashionable.
From Old Hollywood to the present, here are 17 celebrity fashion moments that have sparked debate over the years.
#1 Halle Berry and her swoon-worthy James Bond outfit
Source: © Die Another Day / 20th Century Studios
#2 Lizzy Gardiner wore a credit card dress in 1995
Source: © Ron Galella / Ron Galella Collection / Getty Images
#3 Priyanka Chopra and her epic Met Gala gown, which required two attendants and one bus
Source: Charles Sykes / Invision / AP / East News, Charles Sykes / Invision / AP / East News
#4 Cardi B and her Aphrodite-stepping-out-of-a-shell Grammys gown
Source: Gilbert Flores / Broadimage / Broad Image / East News
#5 Madonna in her boy-toy attire at the 1984 MTV Video Music Awards
Source: ASSOCIATED PRESS / East News
#6 Angelina Jolie and her revealing black vinyl dress
Source: © Mr. & Mrs. Smith / 20th Century Studios
#7 Cher in her transparent black Oscar gown in 1988
Source: AP / East News
#8 Gwyneth Paltrow and her controversial 2002 Vanity Fair Oscar gown
Source: Mary Evans / Allstar / Graham Whitby Boot / East News
#9 Lara Flynn Boyle and her ballerina outfit in 2003
Source: Courtesy Everett Collection / East News
#10 Princess Diana with her stunning silk slip floor-length gown at the 1996 Met Gala
Source: © Steve Eichner / WireImage / Getty Images
#11 Barbra Streisand with her see-through gown at the 1969 Academy Awards
Source: ASSOCIATED PRESS / East News
#12 Anne Hathaway and a contentious Oscar gown from 2013.
Source: John Shearer / Invision / AP / East News
#13 Kim Basinger and her Frankenstein-like Oscars gown with Cyrillic characters on her sleeve in 1990
Source: © Alan Light / Wikimedia Commons, © CC BY 2.0
#14 Rihanna with her provocative gown in 2011.
Source: KENNELL KRISTA / SIPA / East News
#15 Zendaya with her silver breastplate dress from 2020
Source: Hahn Lionel / ABACA / Abaca / East News
#16 Brad Pitt in a skirt during a film premiere
Source: babiradpicture / RalfMuelle / SIPA / SIPA / East News
#17 Jordan Roth and his gleaming appearance in 2022
Source: Invision / Invision / East News